Buchwald–Hartwig amination: 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide → 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)-4-pyridinyl]amino]-N-methylbenzamide
81% yield, run at 110 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide | C₁₃H₁₁Cl₂N₃O | |
| Reactant | 2-Methoxy-4-morpholinoaniline | C₁₁H₁₆N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)-4-pyridinyl]amino]-N-methylbenzamide | C₂₄H₂₆ClN₅O₃ | 81.43% |
Conditions
- Temperature
- 110 °C
Yield
- 81% of 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)-4-pyridinyl]amino]-N-methylbenzamide.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
2-methoxy-4-morpholinoaniline (158 mg, 0.76 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (150 mg, 0.51 mmol),diacetoxypalladium (5.69 mg, 0.03 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.3 mg, 0.05 mmol) and cesium carbonate (330 mg, 1.01 mmol) were weighed out in a microwave vial and sealed. dioxane (3 mL) was added and argon was let to bubble for 5 minutes at rt. The resulting mixture was stirred at 110 °C for 1 hour. The reaction mixture was allowed to cool to room temperature and concentrated in presence of decalite speed plus. The crude product was purified by flash chromatography on silica gel eluting with 0 to 4% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness. The foam was triturated in terbutyl methyl ether and the
The source
This record comes from experimental reaction archive (ord-3d64643dd74a4d9290119a9c4f05506f). Open the source and check it against what is on this page.
experimental reaction archive record ord-3d64643dd74a4d9290119a9c4f05506f from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
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